Chromophore

A chromophore is a molecule which

absorbs light at a particular wavelength
and emits color as a result. Chromophores
are commonly referred to as colored
molecules for this reason. The word is
derived from "chromo-," which means
color, and "-phore," which means "carrier
of." Many molecules in nature are
chromophores, including chlorophyll, the
molecule responsible for the green colors
of leaves. The color that is seen by our
eyes is that of the light not absorbed by
the reflecting object within a certain
wavelength spectrum of visible light. The
chromophore indicates a region in the
molecule where the energy difference
between two separate molecular orbitals
falls within the range of the visible
spectrum (or in informal contexts, the
spectrum under scrutiny). Visible light that
hits the chromophore can thus be
absorbed by exciting an electron from its
ground state into an excited state. In
biological molecules that serve to capture
or detect light energy, the chromophore is
the moiety that causes a conformational
change in the molecule when hit by light.

Leaves change color in the fall

because their chromophores
(chlorophyll molecules) break down
and stop absorbing red and blue
light.[1]

Healthy plants are perceived as green

because chlorophyll absorbs mainly
the blue and red wavelengths but
green light, reflected by plant
structures like cell walls, is less
absorbed.[2]

The eleven conjugated double bonds that form the

chromophore of the β-carotene molecule are
highlighted in red.
Conjugated pi-bond system
chromophores

The porphyrin moieties in our red

blood cells, whose primary function is
to bind iron atoms which capture
oxygen, result in the heme
chromophores which give human
blood its red color. Heme is degraded
by the body into biliverdin (which
gives bruises their blue-green color),
which in turn is degraded into bilirubin
(which gives patients with jaundice a
yellow skin tone).
 In the human eye, the molecule retinal is a
conjugated chromophore. Retinal begins as 11-cis-
retinal, which, upon capturing a photon γ (light) of
the correct wavelength, straightens out into all-
trans-retinal which pushes against an opsin protein
in the retina, which triggers a chemical signaling
cascade which results in perception of light or
images by the human brain.

Just like how two adjacent p-orbitals in a

molecule will form a pi-bond, three or more
adjacent p-orbitals in a molecule can form
a conjugated pi-system. In a conjugated pi-
system, electrons are able to capture
certain photons as the electrons resonate
along a certain distance of p-orbitals -
similar to how a radio antenna detects
photons along its length. Typically, the
more conjugated (longer) the pi-system is,
the longer the wavelength of photon can
be captured. In other words, with every
added adjacent double bond we see in a
molecule diagram, we can predict the
system will be progressively more likely to
appear yellow to our eyes as it is less likely
to absorb yellow light and more likely to
absorb red light. ("Conjugated systems of
fewer than eight conjugated double bonds
absorb only in the ultraviolet region and
are colorless to the human eye",
"Compounds that are blue or green
typically do not rely on conjugated double
bonds alone.")[3]
In the conjugated chromophores, the
electrons jump between energy levels that
are extended pi orbitals, created by
electron clouds like those in aromatic
systems. Common examples include
retinal (used in the eye to detect light),
various food colorings, fabric dyes (azo
compounds), pH indicators, lycopene, β-
carotene, and anthocyanins. Various
factors in a chromophore's structure go
into determining at what wavelength
region in a spectrum the chromophore will
absorb. Lengthening or extending a
conjugated system with more unsaturated
(multiple) bonds in a molecule will tend to
shift absorption to longer wavelengths.
Woodward–Fieser rules can be used to
approximate ultraviolet-visible maximum
absorption wavelength in organic
compounds with conjugated pi-bond
systems.

Some of these are metal complex

chromophores, which contain a metal in a
coordination complex with ligands.
Examples are chlorophyll, which is used by
plants for photosynthesis and hemoglobin,
the oxygen transporter in the blood of
vertebrate animals. In these two examples,
a metal is complexed at the center of a
tetrapyrrole macrocycle ring: the metal
being iron in the heme group (iron in a
porphyrin ring) of hemoglobin, or
magnesium complexed in a chlorin-type
ring in the case of chlorophyll. The highly
conjugated pi-bonding system of the
macrocycle ring absorbs visible light. The
nature of the central metal can also
influence the absorption spectrum of the
metal-macrocycle complex or properties
such as excited state lifetime.[4][5][6] The
tetrapyrrole moiety in organic compounds
which is not macrocyclic but still has a
conjugated pi-bond system still acts as a
chromophore. Examples of such
compounds include bilirubin and urobilin,
which exhibit a yellow color.
Auxochrome

An auxochrome is a functional group of

atoms attached to the chromophore which
modifies the ability of the chromophore to
absorb light, altering the wavelength or
intensity of the absorption.

Halochromism

Halochromism occurs when a substance

changes color as the pH changes. This is a
property of pH indicators, whose
molecular structure changes upon certain
changes in the surrounding pH. This
change in structure affects a chromophore
in the pH indicator molecule. For example,
phenolphthalein is a pH indicator whose
structure changes as pH changes as
shown in the following table:

Structure

pH 0-8.2 8.2-12

Conditions acidic or near-neutral basic

Color name colorless pink to fuchsia

Color

In a pH range of about 0-8, the molecule

has three aromatic rings all bonded to a
tetrahedral sp3 hybridized carbon atom in
the middle which does not make the π-
bonding in the aromatic rings conjugate.
Because of their limited extent, the
aromatic rings only absorb light in the
ultraviolet region, and so the compound
appears colorless in the 0-8 pH range.
However, as the pH increases beyond 8.2,
that central carbon becomes part of a
double bond becoming sp2 hybridized and
leaving a p orbital to overlap with the π-
bonding in the rings. This makes the three
rings conjugate together to form an
extended chromophore absorbing longer
wavelength visible light to show a fuchsia
color.[7] At pH ranges outside 0-12, other
molecular structure changes result in
other color changes; see Phenolphthalein
details.

Common chromophore
absorption wavelengths
Functional group or compound Absorption wavelength

Bromophenol blue (yellow form) 591 nm[8]

Malachite green 617 nm[9]

Cyanidin 545 nm

β-carotene 452 nm

See also

Biological pigment
Chromatophore
Fluorophore
Litmus
 Pharmacophore
Photophore, glandular organ
Pigment
Spectroscopy
Visual phototransduction
Woodward's rules

References

1. Kräutler, Bernhard (26 February 2016).

"Breakdown of Chlorophyll in Higher
Plants—Phyllobilins as Abundant, Yet
Hardly Visible Signs of Ripening,
Senescence, and Cell Death" (https://www.
ncbi.nlm.nih.gov/pmc/articles/PMC49503
23) . Angew. Chem. Int. Ed. 4882 (55):
 4882–4907. doi:10.1002/anie.201508928
(https://doi.org/10.1002%2Fanie.2015089
28) . PMC 4950323 (https://www.ncbi.nl
m.nih.gov/pmc/articles/PMC4950323) .
PMID 26919572 (https://pubmed.ncbi.nl
m.nih.gov/26919572) .
2. Virtanen, Olli; Constantinidou, Emanuella;
Tyystjärvi, Esa (2020). "Chlorophyll does
not reflect green light – how to correct a
misconception" (https://doi.org/10.1080%
2F00219266.2020.1858930) . Journal of
Biological Education: 1–8.
doi:10.1080/00219266.2020.1858930 (htt
ps://doi.org/10.1080%2F00219266.2020.1
858930) .
3. Lipton, Mark (Jan 31, 2017). "Chapter 1:
Electronic Structure and Chemical
 Bonding, Chapter 1.10: Pi Conjugation" (htt
ps://chem.libretexts.org/Courses/Purdue/
Purdue%3A_Chem_26505%3A_Organic_C
hemistry_I_(Lipton)/Chapter_1._Electronic
_Structure_and_Chemical_Bonding/1.10%
3A_Pi_Conjugation) . Purdue: Chem
26505: Organic Chemistry I (Lipton),
LibreTexts edition. Purdue University.
4. Gouterman, Martin (2012). "Optical
spectra and electronic structure of
porphyrins and related rings" (https://book
s.google.com/books?id=vuWERW37obgC
&pg=PA1) . In Dolphin, David (ed.). The
Porphyrins V3. Physical Chemistry, Part A.
Elsevier. pp. 1–165. doi:10.1016/B978-0-
12-220103-5.50008-8 (https://doi.org/10.1
016%2FB978-0-12-220103-5.50008-8) .
 ISBN 978-0-323-14390-5.
NAID 10005456738 (https://ci.nii.ac.jp/nai
d/10005456738/en/) .
5. Scheer, Hugo (2006). "An Overview of
Chlorophylls and Bacteriochlorophylls:
Biochemistry, Biophysics, Functions and
Applications". Chlorophylls and
Bacteriochlorophylls. Advances in
Photosynthesis and Respiration. Vol. 25.
pp. 1–26. doi:10.1007/1-4020-4516-6_1 (h
ttps://doi.org/10.1007%2F1-4020-4516-6_
1) . ISBN 978-1-4020-4515-8.
6. Shapley, Patricia (2012). "Absorbing light
with organic molecules" (http://butane.che
m.uiuc.edu/pshapley/GenChem2/B2/1.ht
ml) .
7. Clark, Jim (May 2016). "UV-Visible
Absorption Spectra" (http://www.chemgui
de.co.uk/analysis/uvvisible/theory.html#t
op) . chemguide.co.uk.
8. Harris, C. Daniel (2016). Quantitative
chemical analysis (9 ed.). New York:
Freeman. p. 437. ISBN 9781464135385.
9. Pretsch, Ernö. (1989). Tables of Spectral
Data for Structure Determination of
Organic Compounds (https://www.worldc
at.org/oclc/851381738) . Thomas Clerc,
Joseph Seibl, Wilhelm Simon
(Second ed.). Berlin, Heidelberg: Springer
Berlin Heidelberg. ISBN 978-3-662-10207-
7. OCLC 851381738 (https://www.worldca
t.org/oclc/851381738) .
External links

Causes of Color (http://webexhibits.org/

causesofcolor/index.html) : physical
mechanisms by which color is
generated.
High Speed Nano-Sized Electronics May
be Possible with Chromophores (https://
web.archive.org/web/20060805192201/
http://www.azonano.com/news.asp?ne
wsID=2538) - Azonano.com

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